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<meta name="citation_title" content="Gly-Ser-Ser-Lys-(FITC)-Gly-Gly-Gly-Cys-Arg-Gly-Asp-Cys-CLIO-Cy5.5">
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<meta name="citation_author" content="Huiming Zhang">
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<meta name="description" content="The αυβ3 integrin, also known as the vitronectin receptor, is a heterodimeric transmembrane glycoprotein found on most cells originating from mesenchyme (1). This receptor is often overexpressed in various tumor cells, including osteosarcomas, neuroblastomas, glioblastomas, invasive melanomas, and carcinomas of the lung, breast, prostate, and bladder (1). Many extracellular matrix proteins such as fibronectin, vitronectin, thrombospondin, fibrinogen, osteopontin, and tenascin are known to be involved in interactions with various subtypes of integrins (1). These proteins may contain a variety of motifs for potential cell binding; however, one of the most frequent cell-recognition motifs includes an amino acid sequence of Arg-Gly-Asp (RGD), called “the universal cell-recognition site” (1) or “a versatile cell recognition signal” (2). The binding potency of the RGD motif leads to the development of small homing peptides, whose high affinity to the αυβ3 integrin provides a promising alternative to antibodies in targeting tumors (3). As a result, RGD analogs are widely used in tumor imaging, anti-angiogenesis treatment, and tumor-associated radionucleotides or chemotherapeutic drugs. Some RGD analogs are currently being used in phase II clinical trials (4). These αυβ3 integrin–specific probes will help oncologists improve the delineation of tumors and follow up the progression of anti-angiogenic therapies (4).">
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<meta name="og:description" content="The αυβ3 integrin, also known as the vitronectin receptor, is a heterodimeric transmembrane glycoprotein found on most cells originating from mesenchyme (1). This receptor is often overexpressed in various tumor cells, including osteosarcomas, neuroblastomas, glioblastomas, invasive melanomas, and carcinomas of the lung, breast, prostate, and bladder (1). Many extracellular matrix proteins such as fibronectin, vitronectin, thrombospondin, fibrinogen, osteopontin, and tenascin are known to be involved in interactions with various subtypes of integrins (1). These proteins may contain a variety of motifs for potential cell binding; however, one of the most frequent cell-recognition motifs includes an amino acid sequence of Arg-Gly-Asp (RGD), called “the universal cell-recognition site” (1) or “a versatile cell recognition signal” (2). The binding potency of the RGD motif leads to the development of small homing peptides, whose high affinity to the αυβ3 integrin provides a promising alternative to antibodies in targeting tumors (3). As a result, RGD analogs are widely used in tumor imaging, anti-angiogenesis treatment, and tumor-associated radionucleotides or chemotherapeutic drugs. Some RGD analogs are currently being used in phase II clinical trials (4). These αυβ3 integrin–specific probes will help oncologists improve the delineation of tumors and follow up the progression of anti-angiogenic therapies (4).">
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id="jr-fip-info-p"><a id="jr-fip-prev" class="wsprkl btn" title="Jump to previuos match">◀</a><button id="jr-fip-matches">no matches yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK23450_"><span class="title" itemprop="name">Gly-Ser-Ser-Lys-(FITC)-Gly-Gly-Gly-Cys-Arg-Gly-Asp-Cys-CLIO-Cy5.5 </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">cRGD-CLIO(Cy5.5)</div><p class="contribs">Zhang H.</p><p class="fm-aai"><a href="#_NBK23450_pubdet_">Publication Details</a></p></div></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figcRGDCLIOT1"><a href="/books/NBK23450/table/cRGD-CLIO.T1/?report=objectonly" target="object" title="Table" class="img_link icnblk_img" rid-ob="figobcRGDCLIOT1"><img class="small-thumb" src="/corehtml/pmc/css/bookshelf/2.26/img/table-icon.gif" alt="Table Icon" /></a><div class="icnblk_cntnt"><h4 id="cRGD-CLIO.T1"><a href="/books/NBK23450/table/cRGD-CLIO.T1/?report=objectonly" target="object" rid-ob="figobcRGDCLIOT1">Table</a></h4><p class="float-caption no_bottom_margin">
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</p></div></div><div id="cRGD-CLIO.Background"><h2 id="_cRGD-CLIO_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(cRGD-CLIO)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The α<sub>υ</sub>β<sub>3</sub> integrin, also known as the vitronectin receptor, is a heterodimeric transmembrane glycoprotein found on most cells originating from mesenchyme (<a class="bibr" href="#cRGD-CLIO.REF.1" rid="cRGD-CLIO.REF.1">1</a>). This receptor is often overexpressed in various tumor cells, including osteosarcomas, neuroblastomas, glioblastomas, invasive melanomas, and carcinomas of the lung, breast, prostate, and bladder (<a class="bibr" href="#cRGD-CLIO.REF.1" rid="cRGD-CLIO.REF.1">1</a>). Many extracellular matrix proteins such as fibronectin, vitronectin, thrombospondin, fibrinogen, osteopontin, and tenascin are known to be involved in interactions with various subtypes of integrins (<a class="bibr" href="#cRGD-CLIO.REF.1" rid="cRGD-CLIO.REF.1">1</a>). These proteins may contain a variety of motifs for potential cell binding; however, one of the most frequent cell-recognition motifs includes an amino acid sequence of Arg-Gly-Asp (RGD), called “the universal cell-recognition site” (<a class="bibr" href="#cRGD-CLIO.REF.1" rid="cRGD-CLIO.REF.1">1</a>) or “a versatile cell recognition signal” (<a class="bibr" href="#cRGD-CLIO.REF.2" rid="cRGD-CLIO.REF.2">2</a>). The binding potency of the RGD motif leads to the development of small homing peptides, whose high affinity to the α<sub>υ</sub>β<sub>3</sub> integrin provides a promising alternative to antibodies in targeting tumors (<a class="bibr" href="#cRGD-CLIO.REF.3" rid="cRGD-CLIO.REF.3">3</a>). As a result, RGD analogs are widely used in tumor imaging, anti-angiogenesis treatment, and tumor-associated radionucleotides or chemotherapeutic drugs. Some RGD analogs are currently being used in phase II clinical trials (<a class="bibr" href="#cRGD-CLIO.REF.4" rid="cRGD-CLIO.REF.4">4</a>). These α<sub>υ</sub>β<sub>3</sub> integrin–specific probes will help oncologists improve the delineation of tumors and follow up the progression of anti-angiogenic therapies (<a class="bibr" href="#cRGD-CLIO.REF.4" rid="cRGD-CLIO.REF.4">4</a>).</p><p>Gly-Ser-Ser-Lys-(FITC)-Gly-Gly-Gly-Cys-Arg-Gly-Asp-Cys-cross-linked iron oxide-Cy5.5 (cRGD-CLIO(Cy5.5)) is a magneto-fluorescent nanoparticle for multimodal imaging of α<sub>υ</sub>β<sub>3</sub> integrin. This agent consists of three components: an RGD peptide for targeting α<sub>υ</sub>β<sub>3</sub> integrin, two fluorescence probes for optical detection/imaging, and an iron oxide nanoparticle core for magnetic resonance imaging (MRI) contrast enhancement (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). The peptide contains 12 amino acids with an intramolecular disulfide bond to form a cyclic RGD (cRGD). One of the fluorescence probes, fluorescein isothiocyanate (FITC), is attached to the peptide before conjugation to the nanoparticle, allowing for the characterization of peptide/iron ratio and the quantification of cell-associated peptide or peptide-nanoparticle on the basis of the absorption at 493 nm. The other fluorescence probes (i.e., Cy5.5 or Cy3.5) are cyanine dyes consisting of two quaternized heteroaromatic bases (A and A’) joined by a polymethine chain with five (Cy5.5) or three (Cy3.5) carbons (<a class="bibr" href="#cRGD-CLIO.REF.6" rid="cRGD-CLIO.REF.6">6</a>) and directly bound to the nanoparticle (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). These dyes have a cationic character because of the delocalized positive charge of the chromophore, and they possess high quantum yield, good chemical stability, easy conjugation, and high sensitivity (mole extinction coefficient ~ 250,000 mol/cm) (<a class="bibr" href="#cRGD-CLIO.REF.7" rid="cRGD-CLIO.REF.7">7</a>, <a class="bibr" href="#cRGD-CLIO.REF.8" rid="cRGD-CLIO.REF.8">8</a>). The excitation/emission wavelength is 674/692 nm for Cy5.5 and 548/563 nm for Cy3.5, where hemoglobin and water have their lowest absorption coefficient. The difference in wavelength of Cy5.5/Cy3.5 allows for dual wavelength ratio imaging to quantify the components labeled with Cy5.5 or Cy3.5 (<a class="bibr" href="#cRGD-CLIO.REF.9" rid="cRGD-CLIO.REF.9">9</a>).</p><p>The nanoparticle contains an icosahedral core of superparamagnetic crystalline Fe<sub>3</sub>O<sub>4</sub> (magnetite) (<a class="bibr" href="#cRGD-CLIO.REF.10" rid="cRGD-CLIO.REF.10">10</a>) that is caged by epichlorohydrin cross-linked dextran and functionalized with amine groups (CLIO-NH<sub>2</sub>) (<a class="bibr" href="#cRGD-CLIO.REF.11" rid="cRGD-CLIO.REF.11">11</a>). These amino groups are used in further conjugation chemistry for attaching the RGD peptides and the fluorescent dyes. The superparamagnetic crystalline includes a sufficiently large single-domain of unpaired spins to generate a net magnetic moment that is larger than the sum of its individual unpaired electrons (<a class="bibr" href="#cRGD-CLIO.REF.10" rid="cRGD-CLIO.REF.10">10</a>, <a class="bibr" href="#cRGD-CLIO.REF.12" rid="cRGD-CLIO.REF.12">12</a>). The main difference between these superparamagnetic nanoparticles and paramagnetic ions such as gadolinium (Gd) is their large magnetic moment unhindered by lattice orientation (<a class="bibr" href="#cRGD-CLIO.REF.13" rid="cRGD-CLIO.REF.13">13</a>). Thus, they possess a high magnetic susceptibility that results in a significant induced magnetization inside a magnetic field. This, in turn, creates microscopic field gradients that diphase nearby protons and cause T<sub>2</sub> shortening (<a class="bibr" href="#cRGD-CLIO.REF.13" rid="cRGD-CLIO.REF.13">13</a>). CLIO-NH<sub>2</sub> has a magnetite core of ~5 nm with a hydrodynamic diameter of 20 nm (<a class="bibr" href="#cRGD-CLIO.REF.11" rid="cRGD-CLIO.REF.11">11</a>, <a class="bibr" href="#cRGD-CLIO.REF.12" rid="cRGD-CLIO.REF.12">12</a>), which can lead to a three- to four-fold increase in T<sub>1</sub> relaxivity and a five- to six-fold increase in T<sub>2</sub> relaxivity compared to conventional contrast agents such as Gd-diethylenetriamine pentaacetic acid (Gd-DTPA) (<a class="bibr" href="#cRGD-CLIO.REF.10" rid="cRGD-CLIO.REF.10">10</a>). CLIO-NH<sub>2</sub> is suitable for receptor-directed MRI or magnetically labeled cell probe MRI because it is small enough to easily pass through capillary endothelium while retaining superparamagnetism (<a class="bibr" href="#cRGD-CLIO.REF.12" rid="cRGD-CLIO.REF.12">12</a>). Despite its small size, CLIO still exhibits superparamagnetic properties and is detectable at tissue concentrations of only 50 nmol Fe/g tissue (10<sup>13–14</sup> iron particles/g tissue) (<a class="bibr" href="#cRGD-CLIO.REF.10" rid="cRGD-CLIO.REF.10">10</a>).</p></div><div id="cRGD-CLIO.Synthesis"><h2 id="_cRGD-CLIO_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(cRGD-CLIO)+AND+synthesis%0D%0A" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Montet et al. reported a detailed synthesis of cRGD-CLIO(Cy5.5) (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). Initially, a linear RGD peptide GSSK(FI)GGGCRGDC (IRGD) was obtained with the Fmoc method as a C-terminal amide and oxidized <i>via</i> bubbling air to yield a disulfide-linked cRGD peptide in 0.1 M ammonium bicarbonate. The amino-CLIO nanoparticle was synthesized in several steps. The starting material, monocrystalline iron oxide (MION), was synthesized by neutralization of ferrous salts, ferric salts, and dextran with ammonium hydroxide, followed by ultra-filtration (<a class="bibr" href="#cRGD-CLIO.REF.14" rid="cRGD-CLIO.REF.14">14</a>). The obtained MION was cross-linked in strong base with epichlorohydrin and then reacted with ammonia to produce amino-CLIO (CLIO-NH<sub>2</sub>) (<a class="bibr" href="#cRGD-CLIO.REF.14" rid="cRGD-CLIO.REF.14">14</a>). Finally, CLIO-NH<sub>2</sub> was reacted with the N-hydroxysuccinimide ester of Cy5.5 (Amersham Biosciences Corp., Piscataway, NJ), followed by peptide attachment using disuccinimidyl suberimidate to produce cRGD-CLIO(Cy5.5) (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). There were ~250 amines, 8,000 iron atoms, 27 peptides, and 8 Cy5.5 molecules per CLIO-NH<sub>2</sub> nanoparticle.</p></div><div id="cRGD-CLIO.In_Vitro_Studies_Tes"><h2 id="_cRGD-CLIO_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(cRGD-CLIO)+AND+%22in+vitro%22" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The uptake of cRGD-CLIO(Cy5.5) was examined in human breast carcinomas (BT-20) by iron stain or Cy5.5 fluorescence (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). After injection of nanoparticles, iron and fluorescence were broadly distributed through the tumor. The molecular specificity for cRGD-CLIO(Cy5.5) binding to α<sub>υ</sub>β<sub>3</sub> integrin was determined in BT-20 cells (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). First, the 50% effective concentration (EC<sub>50</sub>) of cRGD-CLIO(Cy5.5) was compared with that of IRGD-CLIO(Cy5.5) when they were bound to the BT-20 cells. The EC<sub>50</sub> was found to be 0.0113 μM for the cyclic isomer and 0.4 μM for the linear isomer using a fluorescence-activated cell-sorting (FACS) cytometer. This demonstrated that the cRGD had a 35-fold increase in affinity compared to the linear RGD. Second, the binding affinity of cRGD-CLIO(Cy5.5) was compared with that of a scrambled peptide analog (srcRGD-CLIO(Cy3.5)) by measuring their uptake in the BT-20 tumor. Animals with tumors were euthanized 24 h after intravenous injection of mixed cRGD-CLIO(Cy5.5) and srcRGD-CLIO(Cy3.5) at 5 mg Fe/kg dose, and slices of tissues were imaged with a multichannel fluorescent imager. The Cy5.5/Cy3.5 ratio was found to be 6.5 in the BT-20 tumor and ~1 in the liver or spleen, where a high concentration of nanoparticles accumulated. The distribution of cRGD-CLIO(Cy5.5) in the BT-20 tumor was illustrated with iron staining and fluorescence microscopy, in which both iron and Cy5.5 fluorescence were observed throughout the whole tumor.</p><p>The expression of α<sub>υ</sub>β<sub>3</sub> integrin in rat gliosarcomas (9L) was first examined with cRGD alone by fluorescein immunoassay (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>). The apparent affinity constant of cRGD-CLIO in the 9L cells was very similar to that in the BT-20 cells, but the maximum amount (<i>B</i><sub>max</sub>) of cRGD bound to α<sub>υ</sub>β<sub>3</sub> integrin was 0.16 pmol in the 9L cells, which is about four times lower than the 0.82 pmol in the BT-20 cells. This indicated that expression of the α<sub>υ</sub>β<sub>3</sub> integrin in the 9L tumor was four times less than that in the BT-20 tumors. Then, the binding affinity of cRGD-CLIO(Cy5.5) in the 9L tumors was compared with that of srcRGD-CLIO(Cy3.5). The Cy5.5/Cy3.5 fluorescence ratio was 1.8, which was 3.6 times lower than that in the BT-20 tumor. In addition, the cRGD-CLIO(Cy5.5) was found to have a hydrodynamic diameter of 28 ± 3 nm with a T<sub>2</sub> relaxivity of 111 mM<sup>-1</sup>s<sup>-1</sup> at 4.7 T (<a class="bibr" href="#cRGD-CLIO.REF.5" rid="cRGD-CLIO.REF.5">5</a>).</p></div><div id="cRGD-CLIO.Animal_Studies"><h2 id="_cRGD-CLIO_Animal_Studies_">Animal Studies</h2><div id="cRGD-CLIO.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(cRGD-CLIO)%20+AND++rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>cRGD-CLIO (Cy5.5) was used to examine the expression of α<sub>υ</sub>β<sub>3</sub> integrin in BT-20 tumors (3–4 mm in diameter) implanted in nude mice. Fluorescence reflectance imaging (FRI) was conducted after intravenous injection of cRGD-CLIO(Cy5.5)/srcRGD-CLIO(Cy3.5) at 5 mg Fe/kg. FRI showed a much higher tumor/background ratio at the Cy5.5 channel than at the Cy3.5 channel during the first 1,500 min after injection. Because the blood half-life time of cRGD-CLIO(Cy5.5) was 180 mins, the signal enhancement in the Cy5.5 channel reflected the accumulation of cRGD-CLIO(Cy5.5) in the tumor cells. Fluorescence molecular tomography (FMT) and MRI at 4.7 T were performed after intravenous injection of 3 mg Fe/kg cRGD-CLIO(Cy5.5). FMT images demonstrated different enhancements for deep tumor slices. MRI images exhibited an apparent T<sub>2</sub>-shortening effect caused by cRGD-CLIO(Cy5.5) because the mean tumor T<sub>2</sub> dropped from 77 ms before injection to 66 ms 24 h after injection.</p></div><div id="cRGD-CLIO.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22%20SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28dog%20OR%20rabbit%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="cRGD-CLIO.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(cRGD-CLIO)%20+AND+(primate+non+human)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="cRGD-CLIO.Human_Studies"><h2 id="_cRGD-CLIO_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(cRGD-CLIO)%20+AND+human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p><div id="cRGD-CLIO.NIH_Support"><h3>NIH Support</h3><p>P50 CA86355, R24 CA92782, R01 EB00662</p></div></div><div id="cRGD-CLIO.references"><h2 id="_cRGD-CLIO_references_">References</h2><dl class="temp-labeled-list"><dl class="bkr_refwrap"><dt>1.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.1">Haubner R. , Finsinger D. , Kessler H. Stereoisomeric peptide libaries and peptidomimetics for designing selective inhibitors of the aub3 integrin for a new cancer therapy. <span><span class="ref-journal">Angew. Chem. Int. Ed. Engl. </span>1997;<span class="ref-vol">36</span>:1375–1389.</span></div></dd></dl><dl class="bkr_refwrap"><dt>2.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.2">Ruoslahti E. , Pierschbacher M.D. Arg-Gly-Asp: a versatile cell recognition signal. <span><span class="ref-journal">Cell. </span>1986;<span class="ref-vol">44</span>(4):517–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2418980" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2418980</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>3.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.3">Zitzmann S. , Ehemann V. , Schwab M. Arginine-glycine-aspartic acid (RGD)-peptide binds to both tumor and tumor-endothelial cells in vivo. <span><span class="ref-journal">Cancer Res. </span>2002;<span class="ref-vol">62</span>(18):5139–43.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12234975" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12234975</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>4.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.4">Garanger E. , Boturyn D. , Dumy P. Tumor targeting with RGD peptide ligands-design of new molecular conjugates for imaging and therapy of cancers. <span><span class="ref-journal">Anticancer Agents Med Chem. </span>2007;<span class="ref-vol">7</span>(5):552–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17896915" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17896915</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>5.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.5">Montet X. , Montet-Abou K. , Reynolds F. , Weissleder R. , Josephson L. Nanoparticle imaging of integrins on tumor cells. <span><span class="ref-journal">Neoplasia. </span>2006;<span class="ref-vol">8</span>(3):214–22.</span> [<a href="/pmc/articles/PMC1578521/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1578521</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/16611415" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16611415</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>6.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.6">Ernst L.A. , Gupta R.K. , Mujumdar R.B. , Waggoner A.S. Cyanine dye labeling reagents for sulfhydryl groups. <span><span class="ref-journal">Cytometry. </span>1989;<span class="ref-vol">10</span>(1):3–10.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2917472" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2917472</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>7.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.7">Lin Y. , Weissleder R. , Tung C.H. Novel near-infrared cyanine fluorochromes: synthesis, properties, and bioconjugation. <span><span class="ref-journal">Bioconjug Chem. </span>2002;<span class="ref-vol">13</span>(3):605–10.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12009952" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12009952</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>8.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.8">Ballou B. , Fisher G.W. , Hakala T.R. , Farkas D.L. Tumor detection and visualization using cyanine fluorochrome-labeled antibodies. <span><span class="ref-journal">Biotechnol Prog. </span>1997;<span class="ref-vol">13</span>(5):649–58.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9336985" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9336985</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>9.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.9">Kircher M.F. , Josephson L. , Weissleder R. Ratio imaging of enzyme activity using dual wavelength optical reporters. <span><span class="ref-journal">Mol Imaging. </span>2002;<span class="ref-vol">1</span>(2):89–95.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12920849" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12920849</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>10.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.10">Shen T. , Weissleder R. , Papisov M. , Bogdanov A. Jr, Brady T.J. Monocrystalline iron oxide nanocompounds (MION): physicochemical properties. <span><span class="ref-journal">Magn Reson Med. </span>1993;<span class="ref-vol">29</span>(5):599–604.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8505895" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8505895</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>11.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.11">Josephson L. , Perez J.M. , Weissleder R. Magnetic nanosensors for the detection of oligonucleotide sequences. <span><span class="ref-journal">Angew. Chem. Int. Ed. Engl. </span>2001;<span class="ref-vol">40</span>:3204–06.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/29712059" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 29712059</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>12.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.12">Wang Y.X. , Hussain S.M. , Krestin G.P. Superparamagnetic iron oxide contrast agents: physicochemical characteristics and applications in MR imaging. <span><span class="ref-journal">Eur Radiol. </span>2001;<span class="ref-vol">11</span>(11):2319–31.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11702180" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11702180</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>13.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.13">Bulte J.W. , Brooks R.A. , Moskowitz B.M. , Bryant L.H. Jr, Frank J.A. <span class="ref-title">T1 and T2 relaxometry of monocrystalline iron oxide nanoparticles (MION-46L): theory and experiment </span><span class="ref-journal">Acad Radiol</span> 19985Suppl 1S137–40. [<a href="https://pubmed.ncbi.nlm.nih.gov/9561064" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9561064</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>14.</dt><dd><div class="bk_ref" id="cRGD-CLIO.REF.14">Wunderbaldinger P. , Josephson L. , Weissleder R. <span class="ref-title">Crosslinked iron oxides (CLIO): a new platform for the development of targeted MR contrast agents </span><span class="ref-journal">Acad Radiol</span> 20029Suppl 2S304–6. [<a href="https://pubmed.ncbi.nlm.nih.gov/12188255" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12188255</span></a>]</div></dd></dl></dl></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK23450_pubdet_">Publication Details</h2><h3>Author Information and Affiliations</h3><div class="contrib half_rhythm"><span itemprop="author">Huiming Zhang</span>, PhD<div class="affiliation small">
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National Center for Biotechnology Information, NLM, NIH, Bethesda, MD,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a>
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</div></div><h3>Publication History</h3><p class="small">Created: <span itemprop="datePublished">December 17, 2007</span>; Last Update: <span itemprop="dateModified">January 18, 2008</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="http://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>Zhang H. Gly-Ser-Ser-Lys-(FITC)-Gly-Gly-Gly-Cys-Arg-Gly-Asp-Cys-CLIO-Cy5.5. 2007 Dec 17 [Updated 2008 Jan 18]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></p></div><div class="small-screen-prev"><a href="/books/n/micad/R4-SC-CLIO/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/micad/siGFPCLIO/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobcRGDCLIOT1"><div id="cRGD-CLIO.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23450/table/cRGD-CLIO.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__cRGD-CLIO.T1_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Gly-Ser-Ser-Lys-(FITC)-Gly-Gly-Gly-Cys-Arg-Gly-Asp-Cys-CLIO-Cy5.5</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;"></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">cRGD-CLIO(Cy5.5)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Synonym:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Peptide, small molecule (nanoparticle)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">α<sub>υ</sub>β<sub>3</sub> integrin</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Receptor</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Magnetic resonance imaging (MRI), fluorescence molecular tomography (FMT), fluorescence reflectance imaging (FRI)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal/contrast:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Iron oxides, Cy5.5</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li></ul>
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No structure is available in <a href="http://pubchem.ncbi.nlm.nih.gov" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.</td></tr></tbody></table></div></div></article></div><div id="jr-scripts"><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/libs.min.js"> </script><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.min.js"> </script></div></div>
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